Ruthenium complex-catalyzed N-heterocyclization. Syntheses of N-substituted pyrroles and pyrrolidines from 1, 4-diols and primary amines.

Y Tsuji, Y Yokoyama, KT Huh, Y Watanabe

Index: Tsuji, Yasushi; Yokoyama, Yasuharu; Huh, Keun-Tae; Watanabe, Yoshihisa Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 9 p. 3456 - 3458

Full Text: HTML

Citation Number: 46

Abstract

2-Butyne-1, 4-diol reacts with aliphatic amines in the presence of a catalytic amount of [RuCl 2 (PPh 3) 3] at 150° C to give N-alkylpyrroles in good yields. 1, 4-Butanediol reacts with aromatic or aliphatic amines to give N-substituted pyrrolidines in excellent yields;[RuCl 2 (PPh 3) 3] and [RuCl 3· nH 2 O–3PBu 3] are the best catalysts for aromatic and aliphatic amines, respectively. The reaction of 2-butene-1, 4-diol with alkyl amines gives a 1: 1 ...